“Whoever has 100 wants 200.” Our sages were well aware of the insatiable appetite we have for money. One who has $1 million may only desire another million, but one who has $100 million is desirous of much more than a measly million.

This helps explain why once a person has their most basic needs met, there’s no correlation between wealth and happiness. Tragically, it’s often those who need it least who are the ones involved in financial wrongdoing. The idea that one has plenty and thus has no need to commit white-collar crime has no relation to reality.

I recall a striking conversation I had with an acquaintance who was starting a business. He well understood that most businesses lose money in the initial years and said he would be thrilled if he made $50,000. I quipped that perhaps in five years, he would be making $2 million. He immediately responded that if he were making $2 million, he’d want five. I found that to be a sad but most insightful comment, reflecting great self-awareness on my acquaintance’s part.

This psychological reality allows us to understand the insane world of professional sports contracts. The recent signing of Edwin Encarnacion by the Cleveland Indians – the team that defeated the Toronto Blue Jays in last year’s American League Championship Series – is a case in point.

I think there’s an important message here. Encarnacion was eligible for free agency, meaning he could sign with any of Major League Baseball’s 30 teams. Nonetheless, he expressed interest in finishing his career in Toronto, and the Blue Jays were greatly interested in signing him. Within a few days of the end of the season, they offered him a four-year, $80-million contract, a nearly 100-per-cent raise over his 2016 salary. But in today’s atmosphere, players are encouraged – by agents, other players and their own egos – to “test the market” and see what the highest bidder will pay. Thus Encarnacion turned down the Jays’ offer, expecting to do better.

Within days, the Jays had signed his replacement, someone not quite as fearsome, nor expensive. But alas, the expected bidding war never materialized, and as the weeks wore on, there was even talk that somehow Encarnacion and the Blue Jays could find a way to make what both claimed they wanted to work. But it wasn’t to be.

Encarnacion signed with Cleveland for three years and $60 million, $20 million less than the team he wanted to play for had offered him. To feel any degree of pity for someone who is making $20 million a year to play a game is ludicrous, and yet I can guarantee that no matter how wealthy one may be, losing $20 million for no good reason (and even for good ones) would bother one immensely.

It was with great insight that our sages ruled that, in theory, when giving charity to a formerly very wealthy person now in need, we must support him to the point of his previous station. Wealth is relative, and those who have far fewer assets are often “wealthier” than those whose assets may be 100 times greater.

Do we all not do the same thing, albeit on a smaller scale? How many times have we done something we really did not want to just because of the money, money we really did not really need? How many who were happy in their home moved to a much bigger home not because they really wanted to, but because someone as successful as them could not be expected to live in a small house?

There’s much we can learn from Encarnacion’s failed signing. And nothing would be more fitting than the Blue Jays defeating the Indians in the 2017 ALCS on the way to a World Series victory.